11 Travel Planning Mistakes You Don’t Know You’re Making

Our quest for the perfect trip—it’s never-ending. We’re brilliant travel planners. We fill spreadsheets with train times and oddly-spelled destinations, hawkishly watch airfares jump up and slide down until one day we pounce. Months of diligence come to a head, revealing in front of our eyes our eternal goal: the perfect travel plan.

But, eventually, even the mightiest travel planner falls.

Whether an experienced traveller or a first-time globetrotter, none of us are free from silly travel planning blunders. And you might not even know it. Next time you’re planning an epic adventure, keep your eyes peeled for these 11 travel planning mistakes:

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1) Booking flights too far (or not far enough) in advance

Meet our travelling couple: Joe and Sally. Joe is a worrywart. He wants every detail planned and wants it done yesterday. Sally, on the other hand, prefers to sort out details on the fly. Their trip isn’t for another eight months: Joe wants to snap up his plane ticket now, Sally, at the last minute. Who’s right?


Thai Airways Airplane

A recent airfare survey shows that the prime booking time for the best airfare is 54 days in advance. That’s slightly less than two months before. (So much for minimalist travel planning!)

Keep in mind that 54 days in advance is an average. When flying to popular destinations—especially international—during high season, the longer in advance, the better. (Think: Europe in the summer or tropical destinations at March Break or during Christmas holidays.)

Whenever you choose to book your flight, avoid the two-week window before departure. For most destinations, you’ll eat up a significant chunk of your travel budget purchasing last-minute flights.

2) Booking flights on the wrong day of the week

This one’s been out of the bag for a while: experts claim that Tuesday and Wednesday are the best days of the week to book airplane tickets. It might not be entirely true.

Airport in Oulu, Finland

While many airlines release sales on these days (with competitors soon following suit), snagging up one of these magical fares may require attacking the opportunity quicker than you might be prepared for. Often, these special fares are completely sold out within hours—or at least for the days you want to travel (funny how that works).

Prepare yourself to grasp that chance to book on the cheapest day with fury: set up daily fare alerts on Kayak and sign up for the promotional newsletters of every airline flying to your desired travel destination.

3) Not booking incognito

Ever notice that after searching for airfares multiple times, they seem to go up, even in a matter of hours—or minutes? I speculate the answer to the question “Do airlines practice price discrimination?” is a clandestine secret that only a few tightly-lipped souls share. Until it’s proven, let’s just follow this rule: eat your cookies before they eat you.

Airport Luggage

When searching for and booking flights, always use an incognito browser window to ensure that your browsing information isn’t used to jack up prices.

(And even if the whole price-fixing speculation ulitmately proves a giant misunderstanding, there’s no harm going incognito when you’re looking to plan the perfect trip.)

4) Ignoring layover times

Once upon a time, airlines would refuse to sell tickets with short layovers. Airfare aggregators have changed that: now it’s up to you to figure out whether you’ll have time to disembark, rush through airport security, even clear customs, or re-check-in while sliding into the gate in due time for your next flight.

The Jewel @ Changi Airport

Always avoid short layovers—even if they’ll save you a bunch of money. Airlines don’t tend to be forgiving to travellers who miss flights because of poor planning, and unless you’d like to be stranded in an airport—or spend money on an empty hotel room at your final destination and a new plane ticket—it’s best to give yourself ample time between flights.

5) Not claiming your frequent flyer miles

Astute travel hackers know: claim your frequent flyer miles for every single flight. And what many travellers don’t realize is that you don’t necessarily need to fly the same airline every time to travel to benefit.

San Diego Harbor and Airport in November

The world’s two major airline alliances—Star Alliance and oneworld—cover the whole globe. Find out which airlines in each alliance fly between your home airport and your favourite destinations, and sign up for one of the airlines’ frequent flyer programs. Even if you end up jetting overseas with a different partner in the same alliance, you can often request that the mileage be added to your account—even retroactively.

6) Improperly-sized backpack

It’s not always obvious until it’s too late, but a backpack that’s too big (or too small) can really take a toll on your body.

Hiking Backpacks

A perfectly fitting travel backpack can spell the difference between an enjoyable first walk in a city and a painful one. Be sure that your hip strap sits firmly on the pelvic bone and bears the weight of the pack when the shoulder straps are loosened. If the burden of the weight after adjustment still falls to your shoulders (or sits incorrectly on the hip), it’s time for a backpack upgrade.

7) Sticking to “official” accommodation

Hostels, hotels, guesthouses, pensions—you’ve probably done them all. But besides these well-advertised and easy-to-book accommodation options, there’s a whole whack of sleeping arrangements you may have never considered.

Ryokan Shimizu in Kyoto, Japan

From homestays to private apartments and couchsurfing to internet-café loungers, the possibilities beyond traditional accommodation are nearly endless. My personal favourite: airbnb, where you can rent full apartments or private rooms for a fraction of the price of similar hotel rooms.

8) Letting your itinerary lead you

Does your travel planning look something like this: hop on a flight, land in a new city, spend one or two nights, hop on a bus, arrive in another city, spend one or two nights, and repeat?

It’s a common practice I’m all too happy to speak out against. (Time and time again.)

If you’re not a rabid destination collector, I commend you. Otherwise, here’s my most precious tidbit of advice: don’t let your itinerary command you.

Go hiking in the Superstition Mountains

Trying to pack too much into a trip is completely counter-productive. You’re not only setting yourself up for travel burnout (yes, this is a thing!), but you’re also not giving each destination the attention it truly deserves. By trying to see and do too much, you actually see and do almost nothing.

Instead of going a mile wide, go a mile deep. Strike up a minimal plan, a rough sketch if you will, and don’t follow it too closely. Travel has the power to surprise and bewilder only if you give it a little time and space.

9) Relying too much on guidebooks

Just as your itinerary shouldn’t dictate your day, neither should a guidebook. As a starting point, guidebooks are fantastic: they decode an otherwise unfamiliar place and make it instantly accessible. But even when fresh off the press (which is not really so fresh), they’re also riddled with errors and, more importantly, omissions.

Rocky Mountain in Spring

Guidebook writers don’t always have the luxury of time, sometimes writing with about as much experience in a place as our voracious destination-hopper above. Needless to say, there’s more to a city than a passing stranger—or even many bonafide locals—could uncover all on their own. Get out there and discover it for yourself.

10) Packing too much

I love airport baggage claims. (Well, at least as long as they don’t empty without my bag on them.)

Watching traveller after traveller risk a hernia to heave their 20kg+ bag onto the tiled floor brings me some sort of weird amusement. An isolated case of schadenfreude, I guess.

Hiker Backpack

Overpacking has to be one of the silliest of all travel blunders. Unless you’re planning to stay for a year—and even then, the ferocity with which some travellers pack is astounding!—try lightening up your load. Learning how to pack light is a virtue that’s well rewarded in better mobility and less pain.

11) Not learning enough of the local language

All of us are guilty of it: hoping English will be enough to get by. And yes—it is usually enough to get by. But we’re intrepid travellers. We want to experience more, don’t we?

Repair Foreign Language Learning Confidence

If you know where you’re going on your next trip well ahead of time, get out your phrasebooks and course books and try to nail down the basics of the local language. With even just half an hour a day, you can make massive strides towards a more fulfilling and less frustrating trip.

Ryan O'Rourke

Ryan O'Rourke is a Canadian traveller, food & drink aficionado, and the founder & editor of Treksplorer. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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